Caffeine (data page)

This page provides supplementary chemical data on caffeine.

Chemical properties

Names
IUPAC names 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
Identifiers
CAS Number	58-08-2
ChEBI	CHEBI:27732
ChEMBL	ChEMBL113
ChemSpider	2424
DrugBank	DB00201
EC Number	200-362-1
IUPHAR/BPS	407
Jmol interactive 3D	Image Image
KEGG	D00528
PubChem	2519
RTECS number	EV6475000
UNII	3G6A5W338E
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYSA-N InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYAW
SMILES O=C2N(c1ncn(c1C(=O)N2C)C)C Cn1cnc2c1c(=O)n(c(=O)n2C)C
Properties
Chemical formula	C8H10N4O2
Molar mass	194.19 g·mol^−1
Appearance	Odorless, white needles or powder
Density	1.23 g/cm^3, solid[1]
Melting point	227 to 228 °C (441 to 442 °F; 500 to 501 K) (anhydrous) 234 to 235 °C (453 to 455 °F; 507 to 508 K) (monohydrate)
Boiling point	178 °C (352 °F; 451 K) (sublimation)
Solubility in water	2.17 g/100 mL (25 °C) 18.0 g/100 mL (80 °C) 67.0 g/100 mL (100 °C)
Acidity (pKa)	−0.13–1.22[2]
Dipole moment	3.64 D (calculated)
Hazards
Safety data sheet	ICSC 0405
EU classification (DSD)	Harmful (Xn)
R-phrases	R22
S-phrases	(S2)
NFPA 704	0 2 0
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	192 mg/kg (rat, oral)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. Caffeine, International Occupational Safety and Health Information Centre (CIS)
2. This is the pK_a for protonated caffeine, given as a range of values included in Harry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of pK_a Values for Pharmaceutical Substances. Academic Press. ISBN 0-12-260833-X.
3. Peters, Josef M. (1967). "Factors Affecting Caffeine Toxicity: A Review of the Literature". The Journal of Clinical Pharmacology and the Journal of New Drugs (7): 131–141.